US2523528A - N' (4-hydroxy-4-isoimidazol-2-yl)sulfonamides and their production - Google Patents
N' (4-hydroxy-4-isoimidazol-2-yl)sulfonamides and their production Download PDFInfo
- Publication number
- US2523528A US2523528A US86408A US8640849A US2523528A US 2523528 A US2523528 A US 2523528A US 86408 A US86408 A US 86408A US 8640849 A US8640849 A US 8640849A US 2523528 A US2523528 A US 2523528A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- weight
- isoimidazol
- parts
- alpha
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229940124530 sulfonamide Drugs 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- -1 ALKALI METAL SALTS Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- PQCLJXVUAWLNSV-UHFFFAOYSA-N 5-Methyl-2,3-hexanedione Chemical compound CC(C)CC(=O)C(C)=O PQCLJXVUAWLNSV-UHFFFAOYSA-N 0.000 description 4
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 4
- 229960004257 sulfaguanidine Drugs 0.000 description 4
- RTACXVKFHPHAGH-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonylguanidine;hydrate Chemical compound O.NC(N)=NS(=O)(=O)C1=CC=C(N)C=C1 RTACXVKFHPHAGH-UHFFFAOYSA-N 0.000 description 3
- 229920006063 Lamide® Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PDQTXMPRJKIGEI-UHFFFAOYSA-N 2,2,5-trimethylhexane-3,4-dione Chemical compound CC(C)C(=O)C(=O)C(C)(C)C PDQTXMPRJKIGEI-UHFFFAOYSA-N 0.000 description 1
- BANWXFSXYBCSAT-UHFFFAOYSA-N 2,5-dimethylhexane-3,4-dione Chemical compound CC(C)C(=O)C(=O)C(C)C BANWXFSXYBCSAT-UHFFFAOYSA-N 0.000 description 1
- RWHQMRRVZJSKGX-UHFFFAOYSA-N 2-oxobutanal Chemical compound CCC(=O)C=O RWHQMRRVZJSKGX-UHFFFAOYSA-N 0.000 description 1
- GDTHVMAIBQVUMV-UHFFFAOYSA-N 2-oxopentanal Chemical compound CCCC(=O)C=O GDTHVMAIBQVUMV-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000012932 acetate dye Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- FFQMAKNMJYWGCX-UHFFFAOYSA-N benzene 1-sulfonylguanidine Chemical compound C1=CC=CC=C1.NC(=N)N=S(=O)=O FFQMAKNMJYWGCX-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 108010057108 condensin complexes Proteins 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940120731 pyruvaldehyde Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Definitions
- This invention relates to N(hydroxy-4-isoimidazol-Z-yl) sulfanilamides and their alkali metal salts and to methods for their preparation.
- N(4 hydroxy-4-isoimidazol-2-yl)sulfanilamides of the invention are represented by the formula e anilamides of the inventionare easily formed by substitution of the alkali metal for the N-hydrogen atom on the sulfonamido group; such salts are valuable because of their solubility in water.
- the compounds of the invention are prepared by the condensation of an aliphatic alpha-diketone with sulfaguanidine or its monohydrate, or with a benzene sulfonyl guanidine which con tains in the para position a substituent capable of being converted into an amino group.
- Typical suitable alpha-diketones are glyoxal, pyruvaldehyde, biacetyl, 2,3- pentanedione, 2 methyl 3,4 pentanedione, alpha-oxo-butyraldehyde, alpha-oxo-valeraldehyde, 2,3 hexanedione, 2,2-dimethyl-3,4,-pentanedione, 3,4 hexanedione, 2,5 dimethyl-3,4- hexanedione, 2,2,5 trimethyl-3,4-hexanedione, and 5-methyl-2,3-hexanedione.
- the condensation reaction between sulfaguanidine and the alpha-diketone is most readily carried out in the presence of a solvent and is facilitated by the use of a small amount of a condensin agent.
- Sulfuric acid is a satisfactory condensing agent.
- N (4 hydroxy-4-isoimidazol-2-yl)sulfanilamides of the invention are fine-crystalline, high-melting, powdered solids, insoluble in the common low molecular weight organic solvents but soluble in aqueous alkali.
- the alkali metal salts of the compounds are prepared by heating a suspension of the powdered sulfonamide in a solvent such as methanol in the presence of an excess of an alkali metal alkoxide such as sodium methoxide.
- the alkali metal salts are-solid powders, soluble in water, very slightly soluble in the lower alcohols, and insoluble in the common hydrocarbon solvents.
- the compounds of the present invention are particularly valuable as intermediates for the preparation of dyestuffs. They may also be used as insecticides, fungicides, and bactericides and may be useful for therapeutic purposes, and as intermediateproducts in the manufacture of therapeutically active substances.
- a water-insoluble, reddish-orange dyestuff suitable for the coloring of acetate rayon fabrics is obtained from the compound of Example I by first reacting the compound of Example I with sodium nitrite in a cold-acidic suspension of the compound to form the diazo salt and then coupling this salt with alpha-naphthol.
- a deep red-colored, water-soluble, wool dye is obtained by coupling the diazo salt of the compound of Example I with 1-naphthylamine-4-sulfonic acid.
- a yellow, water-insoluble, cellulose acetate dye is obtained by coupling alpha-naphthol with the diazo salt of the compound of Example III.
- EXAMPLE IV A mixture of 10 parts by weight of sulfaguanidine, 6 parts by weight of 5-methyl-2,3-hexanedione, 300 parts by weight of glacial acetic acid and 0.5 part by weight of concentrated sulfuric acid are heated at about 90 C. for one hour. The mixture is cooled and filtered to give 12 parts by Weight of N(4-hydroXy-4-isobuty1- 5 methyl 4-isoimidazol-2-yl)sulfanilamide, a light tan crystalline solid, M. P. 272-275 C. dec.
- Brick red is the color of the dyestuff obtained by diazotizing the compound of Example IV with sodium nitrite and coupling the resulting diazo salt with alpha-naphthol.
- alkali metal salts where R and R are selected from the class consisting of hydrogen and alkyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Sept. 26, 1950 N' (4-HYDROXY-4-ISOIM'IDAZOL-2-YL) SUL- FONAMIDES AND THEIR PRODUCTION Jonathan W. Williams, Claymont, and Thurmond A. Williamson, Arden, DeL, assignors to E. I. du Pont de Nemours & Company, Wilmington, DeL, a corporation of Delaware No Drawing. Application April 8, 1949,
' Serial No. 86,408
(01. zen-ease 2 Claims. 1
This invention relates to N(hydroxy-4-isoimidazol-Z-yl) sulfanilamides and their alkali metal salts and to methods for their preparation.
The N(4 hydroxy-4-isoimidazol-2-yl)sulfanilamides of the invention are represented by the formula e anilamides of the inventionare easily formed by substitution of the alkali metal for the N-hydrogen atom on the sulfonamido group; such salts are valuable because of their solubility in water.
The compounds of the invention are prepared by the condensation of an aliphatic alpha-diketone with sulfaguanidine or its monohydrate, or with a benzene sulfonyl guanidine which con tains in the para position a substituent capable of being converted into an amino group.
The alpha-diketones used in the preparation salt of the N (4-hydroxy lisoimidazol-2-yl) sulfof the compounds of the invention are represented by the formula RG=O R'J1=O where R and R are hydrogen or alkyl; preferably the alkyl is loweralkyl, that is 1 to 5 car bon atoms inclusive. Typical suitable alpha-diketones are glyoxal, pyruvaldehyde, biacetyl, 2,3- pentanedione, 2 methyl 3,4 pentanedione, alpha-oxo-butyraldehyde, alpha-oxo-valeraldehyde, 2,3 hexanedione, 2,2-dimethyl-3,4,-pentanedione, 3,4 hexanedione, 2,5 dimethyl-3,4- hexanedione, 2,2,5 trimethyl-3,4-hexanedione, and 5-methyl-2,3-hexanedione.
The condensation reaction between sulfaguanidine and the alpha-diketone is most readily carried out in the presence of a solvent and is facilitated by the use of a small amount of a condensin agent. Sulfuric acid is a satisfactory condensing agent.
The N (4 hydroxy-4-isoimidazol-2-yl)sulfanilamides of the invention are fine-crystalline, high-melting, powdered solids, insoluble in the common low molecular weight organic solvents but soluble in aqueous alkali. I
The alkali metal salts of the compounds are prepared by heating a suspension of the powdered sulfonamide in a solvent such as methanol in the presence of an excess of an alkali metal alkoxide such as sodium methoxide. The alkali metal salts are-solid powders, soluble in water, very slightly soluble in the lower alcohols, and insoluble in the common hydrocarbon solvents.
The compounds of the present inventionare particularly valuable as intermediates for the preparation of dyestuffs. They may also be used as insecticides, fungicides, and bactericides and may be useful for therapeutic purposes, and as intermediateproducts in the manufacture of therapeutically active substances.
The invention will be more readily understood by reference to the followin examples which illustrate typical compounds of the invention, methods for their preparation, and their use.
EXAMPLE I N'(4 ethyl-4-hydro:ty-5-methyl-4-isoimidazol- Z-yl) sulfam'lamide 5 parts by weight of 2,3-pentanedione is added to a solution of 10 parts by weight of sulfaguanidine monohydrate in 300 parts b weight of ethanol. 0.1 part by weight of concentrated sulfuric acid is added to the solution and the liquid is heated under reflux for 30 minutes. The mass is then cooled and filtered. There is obtained 13 parts by weight of yellow-colored v crystalline N (4 ethyl-4-hydroxy-5-methyl-4- isoimidazol-Z-yl)sulfanilamide, melting at 222- A water-insoluble, reddish-orange dyestuff suitable for the coloring of acetate rayon fabrics is obtained from the compound of Example I by first reacting the compound of Example I with sodium nitrite in a cold-acidic suspension of the compound to form the diazo salt and then coupling this salt with alpha-naphthol. A deep red-colored, water-soluble, wool dye is obtained by coupling the diazo salt of the compound of Example I with 1-naphthylamine-4-sulfonic acid.
EXAMPLE II N (4,5-dimethyl-4-hydroxy-4-isoimidazol-2- yl) sulfanilamide 216 parts by weight of sulfaguanidine monohydrate and 80 parts by weight of biacetyl in 600 parts by weight of glacial acetic acid is heated at 90 C. for 30 minutes. The mixture is cooled and filtered to give 208 parts by weight of crystalline N'(4,5 dimethyl-4-hydroxy-4-isoimidazol-2-yl)sulfanilamide as a pale tan powder melting at 260-265" C.
By diazotizing the compound of Example II and coupling it with alpha-naphthol, a yellowbrown dyestuff is obtained; coupling the diazotized compound with 1-naphthylamine-4-sulfonic acid gives a deep red product.
EXAMPLE III N (4-methyl-el-hydroxy-4-isoimida2ol- 2-yl) sulfam'lamide parts by weight of sulfaguanidine monohydrate is dissolved in 100 parts by weight of glacial acetic acid and 10 parts by weight of 30.4% aqueous pyruvic aldehyde is added thereto. The mixture is heated at 60 C. for minutes, cooled and filtered. There is obtained 11 parts by weight of a brown crystalline solid melting at 245 C. with gross decomposition.
A yellow, water-insoluble, cellulose acetate dye is obtained by coupling alpha-naphthol with the diazo salt of the compound of Example III.
EXAMPLE IV A mixture of 10 parts by weight of sulfaguanidine, 6 parts by weight of 5-methyl-2,3-hexanedione, 300 parts by weight of glacial acetic acid and 0.5 part by weight of concentrated sulfuric acid are heated at about 90 C. for one hour. The mixture is cooled and filtered to give 12 parts by Weight of N(4-hydroXy-4-isobuty1- 5 methyl 4-isoimidazol-2-yl)sulfanilamide, a light tan crystalline solid, M. P. 272-275 C. dec.
Brick red is the color of the dyestuff obtained by diazotizing the compound of Example IV with sodium nitrite and coupling the resulting diazo salt with alpha-naphthol.
EXAMPLE V Sodium salt of N '(4,5-dimethyl-4-hydroxy- 4-isoz'midazoZ-2-yl) sulfam'lamide A mixture of 5 parts by weight of N (4,5-dimethyl 4 hydroxy-4-isoimidazol-2-yl) sulfanil- AMONH,
and then alkali metal salts, where R and R are selected from the class consisting of hydrogen and alkyl.
2. A process for the manufacture of a N (4-hydroxy 4-isoimidazol-2-yl) sulfanilamide which comprises heating an alpha-diketone represented by the formula R'-J=O where R and R are from the class consisting of hydrogen and alkyl, with sulfaguanidine to effect condensation of the two compounds.
JONATHAN W. WILLIAMS. THURMOND A. WILLIAMSON.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,357,249 Anderson Aug. 29, 1944. 2,435,002 Hartmann et al. Jan. 27, 1948 FOREIGN PATENTS Number Country Date 521,821 Great Britain May 31, 1940 OTHER REFERENCES Ganapathi, Proceedings Indian Academy of Science, vol. 13 (1941), pages 316-389.
Claims (1)
1. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF N''(4-HYDROXY-4-ISOIMIDAZOL-2-Y)SULFANILAMIDES REPRESENTED BY THE FORMULA AND THEN ALKALI METAL SALTS, WHERE R AND R'' ARE SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND ALKYL.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86408A US2523528A (en) | 1949-04-08 | 1949-04-08 | N' (4-hydroxy-4-isoimidazol-2-yl)sulfonamides and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86408A US2523528A (en) | 1949-04-08 | 1949-04-08 | N' (4-hydroxy-4-isoimidazol-2-yl)sulfonamides and their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2523528A true US2523528A (en) | 1950-09-26 |
Family
ID=22198374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US86408A Expired - Lifetime US2523528A (en) | 1949-04-08 | 1949-04-08 | N' (4-hydroxy-4-isoimidazol-2-yl)sulfonamides and their production |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2523528A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2858309A (en) * | 1956-05-07 | 1958-10-28 | Ciba Pharm Prod Inc | New aminobenzene sulfonamide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB521821A (en) * | 1938-11-28 | 1940-05-31 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
| US2357249A (en) * | 1942-02-10 | 1944-08-29 | American Cyanamid Co | Method of preparing sulphanilyl aryl guanidines |
| US2435002A (en) * | 1942-01-30 | 1948-01-27 | Ciba Pharm Prod Inc | Process for the manufacture of para-aminobenzene-sulphonamidopyrimidines |
-
1949
- 1949-04-08 US US86408A patent/US2523528A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB521821A (en) * | 1938-11-28 | 1940-05-31 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
| US2435002A (en) * | 1942-01-30 | 1948-01-27 | Ciba Pharm Prod Inc | Process for the manufacture of para-aminobenzene-sulphonamidopyrimidines |
| US2357249A (en) * | 1942-02-10 | 1944-08-29 | American Cyanamid Co | Method of preparing sulphanilyl aryl guanidines |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2858309A (en) * | 1956-05-07 | 1958-10-28 | Ciba Pharm Prod Inc | New aminobenzene sulfonamide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ullman et al. | Stable free radicals. VIII. New imino, amidino, and carbamoyl nitroxides | |
| Dodson et al. | The reaction of ketones with halogens and thiourea1 | |
| Benkeser et al. | The reaction of benzylmagnesium chloride and dibenzylmagnesium with pyridine | |
| DE2363635C3 (en) | Process for the production of chromium complexes from metallizable dyes | |
| US2523528A (en) | N' (4-hydroxy-4-isoimidazol-2-yl)sulfonamides and their production | |
| US2371100A (en) | Tavailabl | |
| US3956271A (en) | Process for the production of concentrated solutions of cationic azo dyes | |
| KREUTZBERGER | Condensations with 1, 2-Hydrazinedicarboxamidine. II. 1 2, 2'-Azoimidazoles2 | |
| DE2919447A1 (en) | ANTI-TUMORIC AGENT | |
| Allen et al. | Certain azomethines in the pyrimidazolone series | |
| CA1180015A (en) | Soluble n.sub.2 substituted derivatives of 2,4- diamino-5-benzyl-pyrimidine, process for their preparation and medicaments containing them | |
| US4002424A (en) | Solution of isomer mixture of naphthylazophenylazonaphthyl disulfonate dye | |
| US3992379A (en) | 4-Alkyldioxyalkylene-5-benzylpyrimidines | |
| EP0023022B1 (en) | Coumarine compounds, processes for their manufacture as well as the intermediate products used perse and their utilisation for the dyeing or printing of textiles | |
| Case et al. | The synthesis and chelation properties of oximes of certain 2‐quinolylmethyl and 2‐phenanthrolylmethyl ketones and of various hydrazones of 2‐acetylquinoline and 2‐acetyl‐1, 10‐phenanthroline | |
| US2578290A (en) | Monoazo compounds containing a 4, 6-dihydroxypyrimidine nucleus | |
| DE19535501A1 (en) | Pyridonmethidazo dyes | |
| US4225708A (en) | 2-Sulfamoyl-5-sulfamido-1-naphthols | |
| US2538558A (en) | Sulfanilamidopyrimidine-formaldehyde condensation products | |
| US2538557A (en) | Sulfanilamidopyrimidine-formaldehyde condensation products | |
| Huntress et al. | Identification of Organic Compounds. VI. 1 The Preparation of p-Nitrobenzyl-pyridinium Salts of Aromatic Sulfonic Acids | |
| US2281014A (en) | Aminoarylsulphonamidopyrazolones | |
| CA1051894A (en) | Derivatives of 5-carboxyalkyl-2-iminobarbituric and 5-carboxyalkyl-2-thioxobarbituric acid | |
| SU668617A3 (en) | Solid dyeing preparation | |
| US2437465A (en) | Manufacture of new coloring matters |